EP0743316A3 - Optically active phosphines, their preparation, their metal complexes and their use in asymmetric synthesis - Google Patents

Optically active phosphines, their preparation, their metal complexes and their use in asymmetric synthesis Download PDF

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Publication number
EP0743316A3
EP0743316A3 EP96107261A EP96107261A EP0743316A3 EP 0743316 A3 EP0743316 A3 EP 0743316A3 EP 96107261 A EP96107261 A EP 96107261A EP 96107261 A EP96107261 A EP 96107261A EP 0743316 A3 EP0743316 A3 EP 0743316A3
Authority
EP
European Patent Office
Prior art keywords
optically active
ein
preparation
formula
metal complexes
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP96107261A
Other languages
German (de)
French (fr)
Other versions
EP0743316B1 (en
EP0743316A2 (en
Inventor
Rainer Dr. Stürmer
Lothar Dr. Laupichler
Paul Prof. Dr. Knochel
Falk Langer
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BASF SE
Original Assignee
BASF SE
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP0743316A2 publication Critical patent/EP0743316A2/en
Publication of EP0743316A3 publication Critical patent/EP0743316A3/en
Application granted granted Critical
Publication of EP0743316B1 publication Critical patent/EP0743316B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
    • C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
    • C07C45/505—Asymmetric hydroformylation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0033—Iridium compounds
    • C07F15/004—Iridium compounds without a metal-carbon linkage
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0046—Ruthenium compounds
    • C07F15/0053—Ruthenium compounds without a metal-carbon linkage
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0073—Rhodium compounds
    • C07F15/008—Rhodium compounds without a metal-carbon linkage
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/5018—Cycloaliphatic phosphines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/5027—Polyphosphines

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Die vorliegende Erfindung betrifft optisch aktive Phosphine der allgemeinen Formel I oder II, XnPRm

Figure 80000001
in der die Variablen folgende Bedeutung haben:

X
ein optisch aktiver Terpenrest
R
ein gegebenenfalls substituierter Phenylrest
Y
ein Brückenglied mit 1 - 10 C-Atomen in der Formel I
n
1,2,3
m
0,1,2 mit der Maßgabe, daß n+m=3 in der Formel II
n
1,2
m
0,1 mit der Maßgabe, daß n+m=2, deren Herstellung und Verwendung.
The present invention relates to optically active phosphines of the general formula I or II, X n PR m
Figure 80000001
in which the variables have the following meaning:
X
an optically active terpene residue
R
an optionally substituted phenyl radical
Y
a bridge member with 1 - 10 carbon atoms in the formula I.
n
1,2,3
m
0.1.2 with the proviso that n + m = 3 in formula II
n
1.2
m
0.1 with the proviso that n + m = 2, their production and use.

EP96107261A 1995-05-12 1996-05-08 Optically active phosphines, their preparation, their metal complexes and their use in asymmetric synthesis Expired - Lifetime EP0743316B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19516968 1995-05-12
DE19516968A DE19516968A1 (en) 1995-05-12 1995-05-12 Optically active phosphines, their production, their metal complexes and their use in asymmetric synthesis

Publications (3)

Publication Number Publication Date
EP0743316A2 EP0743316A2 (en) 1996-11-20
EP0743316A3 true EP0743316A3 (en) 1998-04-29
EP0743316B1 EP0743316B1 (en) 2002-11-06

Family

ID=7761450

Family Applications (1)

Application Number Title Priority Date Filing Date
EP96107261A Expired - Lifetime EP0743316B1 (en) 1995-05-12 1996-05-08 Optically active phosphines, their preparation, their metal complexes and their use in asymmetric synthesis

Country Status (4)

Country Link
US (1) US5723642A (en)
EP (1) EP0743316B1 (en)
CA (1) CA2176304C (en)
DE (2) DE19516968A1 (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19619527A1 (en) * 1996-05-15 1997-11-20 Hoechst Ag Catalyst systems based on rhodium complex compounds with diphosphine ligands and their use in the production of aldehydes
DE19544448A1 (en) * 1995-11-29 1997-06-05 Basf Ag Process for the production of methylene-bridged hetero compounds and new bis (diorganylphosphino) methanes
AU5907898A (en) * 1997-01-13 1998-08-03 Penn State Research Foundation, The Asymmetric synthesis and catalysis with chiral heterocyclic compounds
JP4066139B2 (en) * 1999-12-20 2008-03-26 日本化学工業株式会社 1,2-bis (methyl (1,1,3,3-tetramethylbutyl) phosphino) ethane, process for producing the same, transition metal complex using the same as ligand, and use thereof
BR0112128A (en) * 2000-07-03 2003-05-13 Speedel Pharma Ag Process for the preparation of (r) -2-alkyl-3-phenyl-1-propanols
FI20002807A0 (en) * 2000-09-05 2000-12-20 Neste Chemicals Oy A process for the hydroformylation of alkenes

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3403194A1 (en) * 1984-01-31 1985-08-01 Degussa Ag, 6000 Frankfurt OPTICALLY ACTIVE 3,4-BIS (DIPHENYLPHOSPHINO) PYRROLIDINE, THESE RHODIUM COMPLEXES CONTAINING CHIRAL LIGANDS AND THEIR USE
DE3446303A1 (en) * 1984-12-19 1986-06-19 Degussa Ag, 6000 Frankfurt METHOD FOR PRODUCING OPTICALLY ACTIVE 1-BENZYL-3,4-BIS (DIPHENYLPHOSPHINO) PYRROLIDINE
JPS63135397A (en) * 1986-11-27 1988-06-07 Takasago Corp Ruthenium-phosphine complex
JPS63145291A (en) * 1986-12-09 1988-06-17 Takasago Corp Ruthenium-phosphine complex
JP3313805B2 (en) * 1993-03-12 2002-08-12 高砂香料工業株式会社 Phosphine compounds and transition metal-phosphine complexes having the same as ligands

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
"A CATALYZED ASYMMETRIC SYNTHESIS", ANGEWANDTE CHEMIE. INTERNATIONAL EDITION, vol. 11, no. 11, November 1972 (1972-11-01), pages 1023/1024, XP000616646 *
BRUNNER H ET AL: "ASYMMETRISCHE KATALYSEN, 88 1 KINETIK DER RH-KATALYSIERTEN HYDRIERUNG VON (Z)-(ALPHA)-N-ACETYLAMINOSUMTSAEURE MIT OPTISCH AKTIVEN SCHALENPHOSPHINEN ALS LIGANDEN ASYMMETRIC CATALYSIS, 88 1 KINETICS OF THE RH CATALYSED HYDROGENATION OF (Z)-(ALPHA)-N- ACETAMIDOCINNAMIC ACID WITH OPTICALLY ACTIVE LAYER-", ZEITSCHRIFT FUR NATURFORSCHUNG, TEIL B: ANORGANISCHE CHEMIE, ORGANISCHE CHEMIE, vol. 49, no. 9, September 1994 (1994-09-01), pages 1305 - 1307, XP000466909 *
LANGER F ET AL: "A new efficient preparation of polyfunctional phosphines using zinc organometallics", TETRAHEDRON LETT. (TELEAY,00404039);95; VOL.36 (26); PP.4591-4, PHILIPPS UNIV.;FACHBEREICH CHEMIE; MARBURG; D-35032; GERMANY (DE), XP002057218 *
LONGEAU A ET AL: "Preparation and reactions of functionalized chlorodiorganophosphine-borane complexes using organozinc reagents", TETRAHEDRON LETT. (TELEAY,00404039);96; VOL.37 (13); PP.2209-12, FACHBEREICH CHEM. PHILIPPS-UNIV. MARBURG;MARBURG; D-35032; GERMANY (DE), XP002057219 *

Also Published As

Publication number Publication date
EP0743316B1 (en) 2002-11-06
US5723642A (en) 1998-03-03
DE59609845D1 (en) 2002-12-12
DE19516968A1 (en) 1996-11-14
CA2176304C (en) 2007-01-09
EP0743316A2 (en) 1996-11-20
CA2176304A1 (en) 1996-11-13

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